HU201537B - Process for producing 2-chloro-5-chloromethylthiazole - Google Patents

Process for producing 2-chloro-5-chloromethylthiazole Download PDF

Info

Publication number: HU201537B
Authority: HU; Hungary
Prior art keywords: chlorine; chloro; chloromethylthiazole; formula; reaction
Prior art date: 1986-09-17

Application number

HU874134A

Other languages

English (en)

Hungarian (hu)

Other versions

HUT48225A (en

Inventor

Guenther Beck

Helmut Heitzer

Original Assignee

Bayer Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-09-17

Filing date

1987-09-17

Publication date

1990-11-28

1987-09-17 Application filed by Bayer Ag filed Critical Bayer Ag

1989-05-29 Publication of HUT48225A publication Critical patent/HUT48225A/hu

1990-11-28 Publication of HU201537B publication Critical patent/HU201537B/hu

Links

VRMUIVKEHJSADG-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=CN=C(Cl)S1 VRMUIVKEHJSADG-UHFFFAOYSA-N 0.000 title claims description 25
238000000034 method Methods 0.000 title claims description 10
ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 claims description 32
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 28
229910052801 chlorine Inorganic materials 0.000 claims description 28
239000000460 chlorine Substances 0.000 claims description 28
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
235000016720 allyl isothiocyanate Nutrition 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 5
239000012320 chlorinating reagent Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
238000009987 spinning Methods 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims 1
229960001701 chloroform Drugs 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 13
238000004817 gas chromatography Methods 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000010992 reflux Methods 0.000 description 9
238000005660 chlorination reaction Methods 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
239000000047 product Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000007789 gas Substances 0.000 description 6
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
-1 5-ethoxycarbonylthiazole lithium aluminum hydride Chemical compound 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
239000012071 phase Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000005194 fractionation Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000001577 simple distillation Methods 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000005086 pumping Methods 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
PFBUOGLTNALCPX-UHFFFAOYSA-N (2-chloro-1-oxopropan-2-yl) acetate Chemical compound CC(=O)OC(C)(Cl)C=O PFBUOGLTNALCPX-UHFFFAOYSA-N 0.000 description 1
WKBQQWDVVHGWDB-UHFFFAOYSA-N 1,3-thiazol-5-ylmethanol Chemical compound OCC1=CN=CS1 WKBQQWDVVHGWDB-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
YNWQHHGSQCQVQD-UHFFFAOYSA-N 5-(chloromethyl)-1,3-thiazol-2-amine Chemical compound NC1=NC=C(CCl)S1 YNWQHHGSQCQVQD-UHFFFAOYSA-N 0.000 description 1
NHRPDSWALNDCIN-UHFFFAOYSA-N 5-(chloromethyl)-2-methyl-1,3-thiazole Chemical compound CC1=NC=C(CCl)S1 NHRPDSWALNDCIN-UHFFFAOYSA-N 0.000 description 1
RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical class Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
239000008164 mustard oil Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Thiazole And Isothizaole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

HU874134A 1986-09-17 1987-09-17 Process for producing 2-chloro-5-chloromethylthiazole HU201537B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863631538 DE3631538A1 (de)	1986-09-17	1986-09-17	Verfahren zur herstellung von 2-chlor-5-chlormethylthiazol

Publications (2)

Publication Number	Publication Date
HUT48225A HUT48225A (en)	1989-05-29
HU201537B true HU201537B (en)	1990-11-28

Family

ID=6309717

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU874134A HU201537B (en)	1986-09-17	1987-09-17	Process for producing 2-chloro-5-chloromethylthiazole

Country Status (8)

Country	Link
US (1)	US4748243A (de)
EP (1)	EP0260560B1 (de)
JP (1)	JPH07116167B2 (de)
KR (1)	KR940011458B1 (de)
CA (1)	CA1306463C (de)
DD (1)	DD263988A5 (de)
DE (2)	DE3631538A1 (de)
HU (1)	HU201537B (de)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5180833A (en)	1990-03-16	1993-01-19	Takeda Chemical Industries, Ltd.	Process for the preparation of chlorothiazole derivatives
IE911168A1 (en) *	1990-04-13	1991-10-23	Takeda Chemical Industries Ltd	Novel intermediates for preparing guanidine derivatives,¹their preparation and use
ATE199714T1 (de) *	1994-11-22	2001-03-15	Abbott Lab	Verfahren zur herstellung von 5-hydroxymethyl- thiazole
EP0850231B1 (de)	1995-09-11	2003-04-02	Syngenta Participations AG	Verfahren zur herstellung von 2-chlor-5-chlomethyl-thiazol-derivaten
GB2305172B (en) *	1995-09-14	1998-11-18	Fine Organics Ltd	Preparation of substituted thiazoles
GB9518824D0 (en) *	1995-09-14	1995-11-15	Fine Organics Ltd	Preparation of substituted thiazoles
DE69607293T2 (de) *	1995-11-22	2000-12-14	Kureha Chemical Industry Co., Ltd.	Verfahren zum Ersatz einer primären Aminogruppe durch Chlor und Verwendung dieses Verfahrens zur Herstellung von 2-Chlor-5-Chlormethylthiazol
DE19548417A1 (de) *	1995-12-22	1997-06-26	Bayer Ag	Verfahren zur Herstellung von 2-Chlor-5-chlormethylthiazol
IN182219B (de) *	1996-02-21	1999-02-06	Kuraray Co
JP2001508452A (ja) *	1997-01-22	2001-06-26	ノバルティスアクチェンゲゼルシャフト	チアゾール誘導体の製造方法
WO1998045279A1 (en) *	1997-04-07	1998-10-15	Reilly Industries, Inc.	Preparation of thiazoles using 1,3-dihalopropenes
US5959118A (en) *	1997-08-29	1999-09-28	Abbott Laboratories	Process for the preparation of 5-hydroxymethylthiazoles
DE19908447A1 (de)	1999-02-26	2000-08-31	Bayer Ag	Verfahren zur Herstellung von 2-Chlor-5-chlormethylthiazol
US6265553B1 (en) *	1999-08-10	2001-07-24	Syngenta Crop Protection, Inc.	Intermediate thiazoles and process for the preparation of 2-chloro-5-chloromethyl-thiazole
AT409760B (de) *	1999-11-15	2002-11-25	Dsm Fine Chem Austria Gmbh	Verfahren zur herstellung von 2-chlor-5-chlormethyl-1,3-thiazol
AT408756B (de) *	2000-05-23	2002-03-25	Dsm Fine Chem Austria Gmbh	Verfahren zur herstellung von 2-chlor-5-chlormethyl-1,3-thiazol
MXPA03001550A (es) *	2000-08-23	2003-06-06	Syngenta Participations Ag	Proceso catalitico para la preparacion de derivados de tiazol.
US6407251B1 (en) *	2000-12-28	2002-06-18	Takeda Chemical Industries, Ltd.	Process for preparing 2-chloro-5-chloromethylthiazole
EP1728787B1 (de) *	2004-03-22	2011-01-26	Toyo Boseki Kabushiki Kaisha	Verfahren zur aufreinigung von 2-chlor-5-chlormethyl-1,3-thiazol
DE102006015467A1 (de)	2006-03-31	2007-10-04	Bayer Cropscience Ag	Substituierte Enaminocarbonylverbindungen
DE102006033572A1 (de)	2006-07-20	2008-01-24	Bayer Cropscience Ag	N'-Cyano-N-halogenalkyl-imidamid Derivate
EP2039678A1 (de)	2007-09-18	2009-03-25	Bayer CropScience AG	Verfahren zum Herstellen von 4-Aminobut-2-enoliden
EP2107058A1 (de)	2008-03-31	2009-10-07	Bayer CropScience AG	Substituierte Enaminothiocarbonylverbindungen
EP2264008A1 (de)	2009-06-18	2010-12-22	Bayer CropScience AG	Substituierte Enaminocarbonylverbindungen
WO2012062740A1 (de)	2010-11-12	2012-05-18	Bayer Cropscience Ag	Verfahren zur herstellung von 2,2-difluorethylamin-derivaten ausgehend von n-(2,2-difluorethyl)prop-2-en-1-amin
CN103755661B (zh) *	2014-02-08	2016-09-21	山东省农药科学研究院	一种2-氯-5-氯甲基噻唑的分离精制方法
CN106749086B (zh) *	2016-12-27	2019-05-24	江苏振方生物化学有限公司	一种农药中间体2-氯-5-氯甲基噻唑的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4013674A (en) *	1974-12-12	1977-03-22	Bayer Aktiengesellschaft	N-(1,2,2,2-tetrachloroethyl)-formimide-chloride for synthesizing trichlorothiazole
JPS545972A (en) *	1977-06-13	1979-01-17	Nissan Chem Ind Ltd	Thiazolecarbameta compunds and herbicides containing the same as active constituents
DE3681465D1 (de) *	1985-02-04	1991-10-24	Nihon Bayer Agrochem K.K., Tokio/Tokyo, Jp

1986
- 1986-09-17 DE DE19863631538 patent/DE3631538A1/de not_active Withdrawn
1987
- 1987-08-31 US US07/091,577 patent/US4748243A/en not_active Expired - Lifetime
- 1987-09-07 EP EP87113029A patent/EP0260560B1/de not_active Expired - Lifetime
- 1987-09-07 DE DE8787113029T patent/DE3762745D1/de not_active Expired - Lifetime
- 1987-09-15 DD DD87306978A patent/DD263988A5/de not_active IP Right Cessation
- 1987-09-15 CA CA000546851A patent/CA1306463C/en not_active Expired - Lifetime
- 1987-09-16 KR KR1019870010255A patent/KR940011458B1/ko not_active Expired - Fee Related
- 1987-09-16 JP JP62229911A patent/JPH07116167B2/ja not_active Expired - Fee Related
- 1987-09-17 HU HU874134A patent/HU201537B/hu not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS6383079A (ja)	1988-04-13
EP0260560B1 (de)	1990-05-16
DE3762745D1 (de)	1990-06-21
DD263988A5 (de)	1989-01-18
HUT48225A (en)	1989-05-29
EP0260560A1 (de)	1988-03-23
CA1306463C (en)	1992-08-18
JPH07116167B2 (ja)	1995-12-13
US4748243A (en)	1988-05-31
KR880003927A (ko)	1988-06-01
DE3631538A1 (de)	1988-03-24
KR940011458B1 (ko)	1994-12-15

Legal Events

Date	Code	Title	Description
2006-06-28	MM4A	Lapse of definitive patent protection due to non-payment of fees

Publication	Publication Date	Title
HU201537B (en)	1990-11-28	Process for producing 2-chloro-5-chloromethylthiazole
HU224038B1 (hu)	2005-05-30	Eljárás szubsztituált tiazolok előállítására
JPS60208954A (ja)	1985-10-21	２，６，９−トリ置換プリン類の製造法
US4769493A (en)	1988-09-06	Process for producing tetrafluorophthalic acid
DE60021286T2 (de)	2005-12-29	Verfahren zur herstellung von pyrazolo[1,5-b]pyridazin-derivaten
EP0147472B1 (de)	1988-10-12	4-chlor-4-methyl-5-methylen-1,3-dioxolan-2-on
JP3364895B2 (ja)	2003-01-08	葉酸の製造法
EP0259663B1 (de)	1991-01-23	Verfahren zur Herstellung von Tetrafluorphthalsäure
US4658034A (en)	1987-04-14	Process for the preparation of 2,6-dichlorobenzoxazole
JPS62198637A (ja)	1987-09-02	１，１，３−トリクロルアセトンの製造方法
CA1202624A (en)	1986-04-01	Process for the preparation of tertiary alkyl cyanides
GB1563360A (en)	1980-03-26	A 4-methyl-imidazole-5-carboxylate and a process for its manufacture
EP0517924B1 (de)	1996-03-20	Neues disulfidderivat
JP3098100B2 (ja)	2000-10-10	２−クロロ−５−アミノメチルピリジン類の製造方法
KR100493933B1 (ko)	2005-06-10	2-메틸-4-이소티아졸린-3-온 및 이의 염의 제조 방법
KR20010049867A (ko)	2001-06-15	4,6-디클로로-5-플루오로피리미딘의 제조방법
JP3064035B2 (ja)	2000-07-12	アミノクロロプリンの製法
DE3023227A1 (de)	1982-01-07	Verfahren zur herstellung von 2-chlor-benzthiazolen
JPH1029981A (ja)	1998-02-03	ヘキサヒドロピリダジン類の製造方法
HU190087B (en)	1986-08-28	Process for preparing 3-phenyl-pyrrole derivatives
JPS5970677A (ja)	1984-04-21	２−クロロベンズチアゾ−ルの製造方法
SK279665B6 (sk)	1999-02-11	Spôsob prípravy 4-metyl-5-(2-chlóralkyl)tiazolu
HU207984B (en)	1993-07-28	Process for producing n-/n-propyl/-n-/2-phenoxy-ethyl/-amine
KR930001338B1 (ko)	1993-02-26	아미노알킬로 치환된 모노올레핀화합물의 제조방법
JPH0336820B2 (de)	1991-06-03